CH308211A - Process for the preparation of a new pyrimidine derivative. - Google Patents
Process for the preparation of a new pyrimidine derivative.Info
- Publication number
- CH308211A CH308211A CH308211DA CH308211A CH 308211 A CH308211 A CH 308211A CH 308211D A CH308211D A CH 308211DA CH 308211 A CH308211 A CH 308211A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- pyrimidine derivative
- new pyrimidine
- aminomethyl
- pyrimidine
- Prior art date
Links
- 150000003230 pyrimidines Chemical class 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 4
- CALXTADWGQNAAM-UHFFFAOYSA-N 5-(aminomethyl)-2-benzylsulfanylpyrimidin-4-amine Chemical compound NCc1cnc(SCc2ccccc2)nc1N CALXTADWGQNAAM-UHFFFAOYSA-N 0.000 claims description 3
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 3
- 239000013078 crystal Substances 0.000 claims description 3
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims description 2
- 229940044683 chemotherapy drug Drugs 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- -1 lithium aluminum hydride Chemical compound 0.000 description 2
- OKQFKUDLHVFDOE-UHFFFAOYSA-N 4-amino-2-benzylsulfanylpyrimidine-5-carbonitrile Chemical compound C1=C(C#N)C(N)=NC(SCC=2C=CC=CC=2)=N1 OKQFKUDLHVFDOE-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000003672 ureas Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung eines neuen Pyrimidinderivates. Gegenstand des vorliegenden Patentes bildet ein Verfahren zur Herstellung eines neuen Pyrimidinderivates, welches dadurch gekenn zeichnet ist, dass man ein Pyrimidinderivat der Formel
EMI0001.0006
in welcher X einen durch Reduktion in die Aminomethylgruppe überführbaren Rest be deutet, mit einem Reduktionsmittel behandelt.
Der Rest X kann beispielsweise in einer Cyanogruppe oder einer Carbamidgruppe be stehen. Im ersteren Falle kann die Cyano- gruppe leicht mit Raney-Nickel und Wasser stoff vorteilhaft in alkoholischem Ammoniak als Lösungsmittel reduziert werden oder auch mit Lithiumaluminiumhydrid in Äther, Tetra- hydrofuran usw.
Die Carbamidogruppe kann mit Hilfe von Alkali-aluminium- oder -borhydriden in die Aminomethylgruppe übergeführt werden.
Das so erhaltene 2-Benzylmercapto-4-amino- 5-aminomethyl-pyrimidin bildet farblose Kri stalle, die bei 116-117 schmelzen. Es soll als Chemotherapeutikum und als Zwischenpro dukt verwendet werden. Beispiel:
12,2 g 2-Benzylmercapto-4-amino-5-cyan- pyrimidin in 100 cm3 abs. Tetrahydrofuran werden langsam zu einer Lösung von 5,8 g Lithiumaluminiumhydrid in 100 cM3 Tetra- hydrofuran zugetropft. Das Ganze wird 24 Stunden stehengelassen, dann mit Wasser versetzt und alkalisch gemacht. Die ausgefal lene Masse wird getrocknet und aiis Petrol- äther umkristallisiert.
Man erhält so das 2- B enzylmercapto-4- amino - 5 - aminomethyl-pyr- imidin in farblosen, bei 116-117 schmelzen den Kristallen.
Process for the preparation of a new pyrimidine derivative. The subject of the present patent is a process for the preparation of a new pyrimidine derivative, which is characterized in that a pyrimidine derivative of the formula
EMI0001.0006
in which X denotes a radical which can be converted into the aminomethyl group by reduction, treated with a reducing agent.
The radical X can be, for example, in a cyano group or a carbamide group. In the former case, the cyano group can easily be reduced with Raney nickel and hydrogen, advantageously in alcoholic ammonia as a solvent, or with lithium aluminum hydride in ether, tetrahydrofuran, etc.
The carbamido group can be converted into the aminomethyl group with the aid of alkali aluminum or borohydrides.
The 2-benzylmercapto-4-amino-5-aminomethyl-pyrimidine thus obtained forms colorless crystals which melt at 116-117. It is intended to be used as a chemotherapeutic agent and as an intermediate product. Example:
12.2 g of 2-benzylmercapto-4-amino-5-cyano-pyrimidine in 100 cm3 of abs. Tetrahydrofuran are slowly added dropwise to a solution of 5.8 g of lithium aluminum hydride in 100 cM3 of tetrahydrofuran. The whole thing is left to stand for 24 hours, then water is added and the mixture is made alkaline. The precipitated mass is dried and recrystallized using petroleum ether.
The 2-benzylmercapto-4-amino-5-aminomethyl-pyrimidine is thus obtained in colorless crystals which melt at 116-117.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH308211T | 1952-06-27 | ||
| CH306509T | 1952-06-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH308211A true CH308211A (en) | 1955-06-30 |
Family
ID=25735173
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH308211D CH308211A (en) | 1952-06-27 | 1952-06-27 | Process for the preparation of a new pyrimidine derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH308211A (en) |
-
1952
- 1952-06-27 CH CH308211D patent/CH308211A/en unknown
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